2-Deoxy-D-lyxo-hexitol | 35910-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Deoxy-D-lyxo-hexitol
• 英文别名: 2-deoxygalactitol；D-arabino-5-deoxy-hexitol；D-arabino-Hexan-1,2,3,4,6-pentaol；D-arabino-5-Desoxy-hexit；5-Desoxy-D-altrit；2-Desoxy-D-lyxo-hexit；2-Deoxy-lyxo-hexose；(2R,3R,4R)-hexane-1,2,3,4,6-pentol
• CAS: 35910-10-2
• 化学式: C₆H₁₄O₅
• 分子量: 166.174
• InChiKey: LWWIYCLYWKAKRR-HSUXUTPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Deoxy-D-lyxo-hexitol 在 丙酮 、 zinc(II) chloride 作用下， 生成 O¹,O²;O³,O⁴-diisopropylidene-D-arabino-5-deoxy-hexitol
  参考文献：
  名称：

  Overend et al., Journal of the Chemical Society, 1951, p. 2062

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-lyxo-(4R,5R,6R)-hept-1-ene-4,5,6,7-tetrol 4,5,6,7-tetraacetate 在 potassium carbonate sodium tetrahydroborate 、 二甲基硫 、 臭氧 作用下， 以 甲醇 、 水 为溶剂， 反应 33.33h， 生成 2-Deoxy-D-lyxo-hexitol
  参考文献：
  名称：

  A stereochemically general synthesis of 2-deoxyhexoses via the asymmetric allylboration of 2,3-epoxy aldehydes

  摘要：

  A stereochemically general strategy for the synthesis of 2-deoxyhexoses is described. This new approach involves the asymmetric allylboration of epoxy aldehydes 12 and 13, prepared via the Sharpless asymmetric epoxidation reaction, as a means of establishing the stereochemistry of the sugar backbone. Thus, the matched double asymmetric allylborations of 12 and 13 using tartrate allylboronates (R,R)- and (S,S)-7, respectively, provide erythro epoxy alcohols 14 and 16 with excellent diastereoselectivity ( > 96:4) and enantioselectivity (greater-than-or-equal-to 96% ee). The mismatched double asymmetric reactions of 12 and 13 using (S,S)- and (R,R)-7, respectively, provided the diastereomeric threo epoxy alcohols 15 and 17 with lower (ca. 75:25) but still synthetically useful selectivity. The enantiomeric purity of the major diastereomer in each of these reactions was determined to be greater than that of the epoxy aldehyde precursors. Epoxy alcohols 14 and 16 were converted with excellent selectivity to the l-arabino (21) and l-xylo (26) tetrols via neighboring group assisted alpha-substitution reactions of the derived phenylurethane derivatives 18 and 23. Stereochemically complementary beta-opening reactions were accomplished by treating primary alcohols 38, 40, 42, and 44 [prepared from 14-17, respectively, by ethoxyethylation of C(4)-OH and removal of the C(7)-tert-butyldiphenylsilyl (TBDPS) ethers] with NaOH in aqueous t-BuOH at reflux. Acid-catalyzed hydrolysis of the C(4)-ethoxyethyl ethers then provided tetrols d-35 (from 14), d-21 (from 15), d-30 (from 16), and d-26 (from 17), each with excellent stereoselectivity. These tetrols were isolated and fully characterized as the tetraacetate derivatives 36, 22, 31, and 27, respectively. These beta-opening reactions proceed by way of an epoxide migration (29 to 33) that inverts the stereochemistry at C(6) and activates C(7) toward nucleophilic attack. It is necessary that the C(4) hydroxyl be protected in three of the four stereoisomeric series to minimize competitive epoxide migration pathways (cf. 29 to 32a). arabino tetrol 21 and lyxo tetrol 30 were converted to 2-deoxyglucose and 2-deoxygalactose, respectively, by a standard ozonolytic sequence and then to 2-deoxyglucitol pentaacetate (45) and 2-deoxygalactitol pentaacetate (46) via NaBH4 reduction of the 2-deoxy sugars, thereby confirming all stereochemical assignments. The epoxide beta-opening technology was also applied to epoxy benzyl ether 47 (prepared from 14) and epoxy BOM ether 49 (deriving from 16). These reactions provide tetrol derivatives 48 and 50, respectively, in which the C(4)- and C(5)-hydroxyl functionality are suitably differentiated for use in subsequent synthetic sequences.

  DOI：

  10.1021/jo00004a053

文献信息

• Multiple Forms of Xylose Reductase in <i>Candida intermedia</i>:  Comparison of Their Functional Properties Using Quantitative Structure−Activity Relationships, Steady-State Kinetic Analysis, and pH Studies
  作者：Bernd Nidetzky、Kaspar Brüggler、Regina Kratzer、Peter Mayr

  DOI：10.1021/jf034426j

  日期：2003.12.1

  The xylose-fermenting yeast Candida intermedia produces two isoforms of xylose reductase: one is NADPH-dependent (monospecific xylose reductase; msXR), and another is shown here to prefer NADH approximately 4-fold over NADPH (dual specific xylose reductase; dsXR). To compare the functional properties of the isozymes, a steady-state kinetic analysis for the reaction d-xylose + NAD(P)H + H(+) <--> xylitol

  木糖发酵酵母假丝酵母产生两种木糖还原酶同工型：一种是NADPH依赖性的（单特异性木糖还原酶； msXR），另一种是NADH优于NADPH（双特异性木糖还原酶； dsXR）的4倍。为了比较同工酶的功能特性，对反应中的d-木糖+ NAD（P）H + H（+）<->木糖醇+ NAD（P）（+）进行了稳态动力学分析，并进行了特异性分析测定一系列常数（k（cat）/ K（醛））的常数，以减少一系列侧链大小不同的醛的还原以及与酶的底物结合口袋的氢键结合能力。dsXR弱结合NAD（P）（+）（K（iNAD +）= 70 microM; K（iNADP +）= 55 microM）和NADH（K（i）= 8 microM）大约与NADPH（K（i）= 14 microM）。msXR显示NADPH和NADP（+）的均匀结合（K（iNADP +）大约为K（iNADPH）= 20 microM）。通过将dsXR的对数k（cat）/
• Haga, Hidehiko; Nakajima, Terumi, Chemical and pharmaceutical bulletin, 1988, vol. 36, p. 1562 - 1564
  作者：Haga, Hidehiko、Nakajima, Terumi

  DOI：——

  日期：——
• D-glycopyranosyl phenylsulfones: Their use in a stereocontrolledsynthesis of cis-2,6-disubstituted tetrahydropyrans (β-d-c-clycosides)
  作者：Jean-Marie Beau、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(00)95049-4

  日期：1985.1
• Carter, Steven R.; Williams, J. Michael; Clamp, John R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2775 - 2778
  作者：Carter, Steven R.、Williams, J. Michael、Clamp, John R.

  DOI：——

  日期：——
• NANOSENSOR FOR SUGAR DETECTION
  申请人：PARK Seung Bum

  公开号：US20100330686A1

  公开（公告）日：2010-12-30

  Nanosensors for carbohydrate detection are disclosed. The nanosensors include a nanoparticle conjugated to one or more boronic acid molecules or derivatives thereof and one or more pH sensitive materials. The nanosensors may be provided on a pH indicator paper in order to quickly assay samples, such as food samples.